1-allyl-1-(1-(((3S,4R)-1-(cyclopentanecarbonyl)-4-hydroxy-4-phenylpyrrolidin-3-yl)methyl)piperidin-4-yl)-3-(4-(trifluoromethyl)benzyl)urea | 1173564-42-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 1-allyl-1-(1-(((3S,4R)-1-(cyclopentanecarbonyl)-4-hydroxy-4-phenylpyrrolidin-3-yl)methyl)piperidin-4-yl)-3-(4-(trifluoromethyl)benzyl)urea
• 英文别名: 1-[1-[[(3S,4R)-1-(cyclopentanecarbonyl)-4-hydroxy-4-phenylpyrrolidin-3-yl]methyl]piperidin-4-yl]-1-prop-2-enyl-3-[[4-(trifluoromethyl)phenyl]methyl]urea
• CAS: 1173564-42-5
• 化学式: C₃₄H₄₃F₃N₄O₃
• 分子量: 612.736
• InChiKey: IMPVMIVUIIFSCA-ZQAZVOLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  44
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  76.1
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  ((3R,4S)-4-((4-(allylamino)piperidin-1-yl)methyl)-3-hydroxy-3-phenylpyrrolidin-1-yl)(cyclopentyl)methanone 、 在 N,N-二异丙基乙胺 作用下， 生成 1-allyl-1-(1-(((3S,4R)-1-(cyclopentanecarbonyl)-4-hydroxy-4-phenylpyrrolidin-3-yl)methyl)piperidin-4-yl)-3-(4-(trifluoromethyl)benzyl)urea
  参考文献：
  名称：

  Studies on the structure–activity relationship of 1,3,3,4-tetra-substituted pyrrolidine embodied CCR5 receptor antagonists. Part 1: Tuning the N-substituents

  摘要：

  A novel series of CCR5 antagonists has been identified, utilizing the lead, nifeviroc, which were further modified based on bioisosteric principles. Lead optimization was pursued by balancing potential toxicity and potency. Potent analogues with low toxic properties were successfully developed by formation of urea and amide bonds at the nitrogen at position 4- of the pyrrolidine ring. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.05.102

文献信息

• [EN] PYROLLIDINE-BASED COMPOUNDS<br/>[FR] COMPOSÉS À BASE DE PYROLLIDINE
  申请人：SHANGHAI TARGETDRUG CO LTD

  公开号：WO2009092293A1

  公开（公告）日：2009-07-30

  A compound of formula (I) or a pharmaceutically acceptable derivative, salt or prodrug thereof, which can inhibit HIV replication.

  一种化合物，其化学式为（I），或其药学上可接受的衍生物、盐或前药，能够抑制HIV的复制。
• Studies on the structure–activity relationship of 1,3,3,4-tetra-substituted pyrrolidine embodied CCR5 receptor antagonists. Part 1: Tuning the N-substituents
  作者：Li Ben、Eric Dale Jones、Enkun Zhou、Chen Li、Dean Cameron Baylis、Shanghai Yu、Miao Wang、Xing He、Jonathan Alan Victor Coates、David Ian Rhodes、Gang Pei、John Joseph Deadman、Xin Xie、Dawei Ma

  DOI：10.1016/j.bmcl.2010.05.102

  日期：2010.7

  A novel series of CCR5 antagonists has been identified, utilizing the lead, nifeviroc, which were further modified based on bioisosteric principles. Lead optimization was pursued by balancing potential toxicity and potency. Potent analogues with low toxic properties were successfully developed by formation of urea and amide bonds at the nitrogen at position 4- of the pyrrolidine ring. (C) 2010 Elsevier Ltd. All rights reserved.